Unable to Upgrade MS SQL Server 2005 to 2008 R2

I'm currently trying to upgrade an instance of SQL Server 2005 Standard 64bit Edition to SQL Server 2008 R2 Standard Edition. The issue I believe that I am having is that the SQL Server 2008 R2 media is MSDN as this has been re-purposed as a test server. Is it possible to upgrade from a fully licensed version of SQL Server to an MDSN license?

But before you begin, the very fist things you need to double check is Windows Installer and .Net Framework. Make very sure they are the latest. They have single handedly bombed more upgrades than anything else.

Just another thought, have you tried to install side by side rather than upgrade in place ? If it is a test server, then that might be an option to see if you can get the media to install.

I know it is not much help, and maybe you have been to those pages before, but might be of some assistance...

It might be complaining because you're attempting to change the edition and upgrade at the same time. If you got he media from MSDN, are you sure it's standard edition and not developer edition? For a test server, Developer edition is fine (it's functionally the same as Enterprise in every way), but you can't install that edition in production (and comply with the license, anyways).

IF the media you're using is developer edition, you might be better off attempting to change the edition first, and then perform the upgrade, in two separate steps. You can use the install GUI to change the edition using the "Edition Upgrade" option in setup:

A complete uninstall/reinstall is the cleanest way to go, but it leaves you without a back-out plan if anything goes wrong or you realize you've forgotten something. I've done upgrades a number of times in the past and never had an issue, though they can sometimes be a bit picky.

That said, would it be possible to install SQL 2008 as a named instance and then migrate everything, re-directing your client applications to the new instance? That's the safest way to go - you don't take down or damage your old instance, so you can always roll back or refer to previous configuration if it's needed. Once your migration is complete, you also have the option of uninstalling your old default instance from the server completely, so you won't be running two forever.

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